m-Chloroperbenzoic acid → HCID 18427291, compound

HRID 1279193Notes

Reaction equation

HRID 1279193 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9][CH2:10][CH3:11])=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9]([CH2:10][CH3:11])=[O:20])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18427287HCID 18427287, compound

Product 1

HCID 18427291HCID 18427291, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 g (0.02 mol) of 2,3-dichloro-5-ethylthiopyridine were reacted with 3.47 g (0.02 mol) of m-chloroperbenzoic acid in 30 ml of methylene chloride by a method similar to Example 1, Precursor β. After the crude product had been purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate=2:1), 1.9 g of product of value were obtained in the form of white crystals. Yield: 42%. m.p.: 78-79° C.; 1H-NMR (d6 dimethyl sulfoxide): δ [ppm]=1.1 (t; CH3); 3.0 and 3.2 (2×m, CH2); 8.35 and 8.6 (2×s, pyr H).

Workup

  1. customAfter the crude product had been purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate=2:1), 1.9 g of product of value
  2. customwere obtained in the form of white crystals

Sources & evidence

ORD record
ord-720ea94ab4cc4e2489c74997fc0d046d
Source dataset
uspto-grants-2002_09
Patent number
US06448205B1

Reaction notes

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